He was privately tutored at Wimbledon, gazetted to the 12th Lancers in 1865, and stationed in Cahir in County Tipperary. He rode his first Winning Race in 1867 at Cork Park. He joined the Lord Lieutenant's staff as an extra Aide de Camp in 1870, where he was based at the Viceregal Lodge in Dublin, was promoted to Captain and left services. Middleton was one of the best and most popular riders in the United Kingdom. When the Empress of Austria hunted in Ireland, he was her pilot. He repeatedly rode the winners over the stiffest steeplechase courses, including the Punchestown (Ireland) Grand National. Besides being distinguished as a horseman, he was a good cricketer, belonging to the Jockey Cricket Club.

His nickname "Bay" was either a reference to his reddish-brown hair, or derived from the name of the winner of the Epsom Derby winner in 1836.

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In 1875, Middleton became engaged to Charlotte Baird, daughter of William Baird, Esq of Eli, whom he married on 25 October 1882, at St. George's, Hanover Square, The couple had one daughter, Violet Georgina, born in 1886.[1][2]

The Empress Elisabeth of Austria visited England, arriving on 2 August 1874, where she met Earl Spencer. When she returned to England in 1876, she visited Lord Spencer at Althorp, and Bay Middleton was asked to "pilot" the Empress. She left England in February 1882 and never hunted in England or Ireland again.

He had an 18-month affair with Lady (Henrietta) Blanche Ogilvy, while she was married to Colonel Henry Hozier. She confided in a letter (made public in August 2002 by her granddaughter, Mary Soames) to another lover that Bay Middleton was the father of her daughter, Clementine Hozier, born 1 April 1885, who was eventually to marry Sir Winston Churchill.

Another writer, Joan Hardwick, had speculated that Clementine had been fathered by Algernon Bertram Freeman-Mitford (1837-1916): Lady Soames dismissed such earlier speculation as "based on anecdote and gossip", which was, unlike the paternity of Middleton, undocumented.

Captain William George Middleton died in the Midland Sportsman's Cup at Lord Willoughby de Broke's estate at Kineton, killed in a fall from his horse at the Parliamentary steeplechase. He was buried in full riding costume at Haselbech, Northamptonshire. His coffin was kept in the parish church, covered with the Union Jack and flanked with lances of the 12th Lancers, Captain Middleton's regiment. A large assembly of mourners gathered to attend the funeral service, which was conducted by the Rev. W. Lloyd, the rector. Among the mourners were the widow and the deceased's only child, a little girl of six. Earl Spencer, Lord and Lady Willoughby de Broke, Sir Saville Crossley, M.P., Mr. Albert Pell, Captain Atherton, Mr. Charles. W. B. Fernie, General Le Quesne, and many others who were well known in the hunting field also attended Middleton's funeral.